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On the reaction of 2-amino-4-thiazoliniminium salts with active methylene compounds

Reaktion von 2-Amino-4-thiazoliniminium-Salzen mit aktivierten Methylenverbindungen

  • Organische Chemie Und Biochemie
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Summary

The easily available 2-amino-4-thiazoliniminium salts6 react with different types of active methylene compounds. Whereas 2-amino-4-cyanomethylene-4,5-dihydrothiazoles13 and14 are formed with malononitrile (11) or ethyl cyanoacetate (12) in the presence of bases, acetyl acetone (15) and ethyl acetic acetate (16) afford 2-amino-thiazolo[4,5-b]pyridines21 and22, resp. The structures of the new compounds13, 14, 21 and22 have been elucidated by means of analytical and spectroscopic methods and confirmed by some chemical reactions.

Zusammenfassung

Durch Reaktion der einfach zugänglichen 2-Amino-4-thiazoliniminium-Salze6 mit Malonsäuredinitril (11) oder Cyanessigsäureethylester (12) in Gegenwart von Basen werden die 2-Amino-4-cyanmethylen-4,5-dihydrothiazole13 bzw.14 gebildet, während mit Acetylaceton (15) und Acetessigsäureethylester (16) auf analoge Weise die 2-Aminothiazolo[4,5-b]pyridine21 bzw.22 entstehen. Die Strukturen der neu dargestellten Verbindungen des Typs13, 14, 21 und22 wurden spektroskopisch abgesichert und durch einige Folgereaktionen bestätigt.

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Authors and Affiliations

  1. Fachbereich Chemie, Fachhochschule Merseburg, D-06217, Merseburg, Germany

    R. Flaig & H. Hartmann

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  1. R. Flaig
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  2. H. Hartmann
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Flaig, R., Hartmann, H. On the reaction of 2-amino-4-thiazoliniminium salts with active methylene compounds. Monatsh Chem 128, 1051–1060 (1997). https://doi.org/10.1007/BF00806970

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  • DOI: https://doi.org/10.1007/BF00806970

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